Westside Vacation Packages 2026 from $571

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Your Westside Vacation

A great way to experience this city is with a customized Westside vacation package. Stay in the neighborhood of Murray Hill, which is great for distilleries and craft breweries, bars and pubs and dining or go someplace else — our package deals are all about you. Jacksonville Equestrian Center, Crystal Springs Park and Bent Creek Golf Course are just a few of the many sights you'll want to check out during your trip to Westside. Browse Expedia's wide range of travel options and start planning your ultimate vacation to Westside now.

The Latest Westside Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Holiday Inn Express Jacksonville Beach by IHG

$571

per person

Dec 12 - Dec 18

found 5 hours ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

9.2/10 Wonderful! (1,007 reviews)

Perfect stay, great location

Reviewed on Oct 10, 2026

Amelia by the South

Save 100% on your flight

$3,257

per person

Dec 26 - Dec 29

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

No reviews

Amelia by the Sea

Save 100% on your flight

$3,284

per person

Dec 26 - Dec 29

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

No reviews

Historic Springfield Apartments by Landing

Urban Core

$891

per person

Dec 30 - Jan 6

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

8/10 Very Good! (1 review)

Good

Reviewed on Aug 10, 2026

Margaritaville Jacksonville Beach

Oceanfront

$664

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

9/10 Wonderful! (4,560 reviews)

Where to stay in Westside

Find the best Westside areas and neighborhoods for the activities you enjoy most. Learn more about Westside

A city skyline with modern skyscrapers, a prominent Wells Fargo building, and a blue bridge over a river.

Downtown Jacksonville

2 out of top 10 points of interest in this area

Historic core with major corporations, Downtown Jacksonville offers diverse culinary and nightlife experiences at The Elbow. Explore attractions like Florida Theatre, TIAA Bank Field, and museums, while enjoying convenient transportation options.

A coastal town at dusk with a prominent clock tower, waterfront, and illuminated buildings.

Amelia City

While visiting Amelia City, you might make a stop by sights like American Beach and Fernandina Beach.

A sunset over a beach with waves and a pier.

Oceanfront

If you're spending some time in Oceanfront, Oceanfront Park and Northeast Florida Beaches are top sights worth seeing.

A river with a bridge, a marina with boats, and a city skyline with high-rise buildings.

Southside

1 out of top 10 points of interest in this area

If you're spending some time in Southside, St. Johns Town Center and Orange Park Place Shopping Center are top sights worth seeing.

A sunset over a beach with fallen trees and a distant shoreline.

American Beach

If you're spending some time in American Beach, American Beach and Spanish Quarter Village are top sights worth seeing.

Westside Hotel Deals

Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station

8001 PARRAMORE ROAD Jacksonville FL

Fully refundable

$92 nightly

$104 total

Nov 8 - Nov 9

Total with taxes and fees

9.4/10 Exceptional! (1,218 reviews)

"Breakfast was very nice."

Reviewed on Oct 10, 2026

Quality Inn Jacksonville - Orange Park near Naval Air Station

4580 Collins Road Jacksonville FL

Fully refundable

$64 nightly

$72 total

Nov 2 - Nov 3

Total with taxes and fees

StudioRes by Marriott Jacksonville Orange Park

8045 Parramore Road Jacksonville FL

Fully refundableReserve now, pay when you stay

$80 nightly

$91 total

Oct 23 - Oct 24

Total with taxes and fees

8.6/10 Excellent! (54 reviews)

"Courteous staff, clean room, good parking"

Reviewed on Oct 10, 2026

See all 3,226 properties in Westside

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Westside attractions

Jacksonville Equestrian Center

7.6/10 (18 reviews)

You can take time to visit Jacksonville Equestrian Center during your travels to Jacksonville. Attend a sporting event in this family-friendly area.

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Florida Yacht Club Marina

Explore the waterfront in Jacksonville with a trip to Florida Yacht Club Marina. Amble around this family-friendly area's riverfront or experience its acclaimed theater scene.

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Ortega Yacht Club Marina

Explore the waterfront in Jacksonville with a trip to Ortega Yacht Club Marina. Amble around the area's riverfront or attend a sporting event.

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Normandy Lane Plaza Shopping Center

You can search for that perfect souvenir at Normandy Lane Plaza Shopping Center during your visit to Jacksonville. Experience the area's lively festivals and great live music.

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Lakeside Park

Lakeside Park is just one of the places to see in Jacksonville, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or attend a sporting event in the area.

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Ringhaver Park

6.0/10 (1 review)

Explore the great outdoors at Ringhaver Park, a lovely green space in Jacksonville. Stroll along the riverfront or attend a sporting event in this family-friendly area.

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Crystal Springs Park

7.4/10 (6 reviews)

After visiting Crystal Springs Park, make a plan to see the other sights and activities in Jacksonville. Experience the acclaimed theater scene or attend a sporting event in this family-friendly area.

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Columbus Park

8.0/10 (1 review)

After visiting Columbus Park, make a plan to see the other sights and activities in Jacksonville. Stroll along the riverfront or attend a sporting event in the area.

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Things to do

Half-Day City Tour in Downtown Jacksonville

$114

per adult

100% of travellers recommend

1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports

1 Hour Jet Ski Rental in Jacksonville, FL Jax Jet Skis

$145

per traveler

90% of travellers recommend

The Escape Game at St. John's Town Center in Jacksonville

$42

per adult

100% of travellers recommend

See all activities in Jacksonville

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Westside Vacations from $571

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Westside Vacation

The Latest Westside Vacation Packages

Holiday Inn Express Jacksonville Beach by IHG

Amelia by the South

Amelia by the Sea

Historic Springfield Apartments by Landing

Margaritaville Jacksonville Beach

Where to stay in Westside

Downtown Jacksonville

Amelia City

Oceanfront

Southside

American Beach

Westside Hotel Deals

Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station

Quality Inn Jacksonville - Orange Park near Naval Air Station

StudioRes by Marriott Jacksonville Orange Park

Stay near popular Westside attractions

Jacksonville Equestrian Center

Florida Yacht Club Marina

Ortega Yacht Club Marina

Normandy Lane Plaza Shopping Center

Lakeside Park

Ringhaver Park

Crystal Springs Park

Columbus Park

Things to do

Half-Day City Tour in Downtown Jacksonville

1 Hour Jet Ski Rental in Jacksonville, FL Jax Jet Skis

The Escape Game at St. John's Town Center in Jacksonville